Timberlake acknowledged in December 2011 that the inspiration for "Cry Me a River" was his ended relationship with Britney Spears.

Timberlake and Scott Storch wrote "Cry Me a River" with Timbaland, who produced the song.[1] Storch found working with Timberlake easy because of the song's meaning.[2] Reporters believed its lyrics were inspired by Timberlake's romantic relationship with American recording artist Britney Spears,[3] which ended in 2002.[4] Timberlake told MTV News, "I'm not going to specifically say if any song is about anybody. I will say writing a couple of songs on the record helped me deal with a couple of things. To me songs are songs. They can stem from things that completely happened to you personally or they can stem from ideas that you think could happen to you."[3] In December 2011, Timberlake admitted that he had written "Cry Me a River" after an argument with Spears: "I was on a phone call that was not the most enjoyable phone call. I walked into the studio and he [Timbaland] could tell I was visibly angry."[5] Timbaland recalled, "I was like, 'Man, don't worry about it' and he was like, 'I can't believe she did that to me' and he was like, 'You were my sun, you were my earth.'"[5]

"Cry Me a River" was released as the second single from Justified.[3]Jive Records serviced the song to contemporary and rhythmic radio in the United States on November 25, 2002.[6][7] On December 23, three remixes were released as a 12-inch single in Canada and France.[8][9] On January 5, 2003, the song was sent to urban contemporary radio stations in the US.[10] It was released as a CD single in Germany on January 23. The single contains the album version of the song and the remixes on its 12-inch single release.[11] A CD single, which included Johnny Fiasco's remix of the song and two additional remixes of "Like I Love You", was released on February 3 and 6 in the United Kingdom and Canada, respectively.[12][13] "Cry Me a River" was released as a CD single in the US on February 18. The single features the album version of the song, its instrumental and four remixes.[14]

Following its release, there was media speculation that Spears had written a song as a response to "Cry Me a River";[3] she denied the rumors, explaining, "You know, it's funny. I read that I wrote this song and I wrote these lyrics and that's not my style. I would never do that."[15]Annet Artani, who co-wrote Spears' 2003 song "Everytime", stated that the song was written as a response to "Cry Me a River".[16] When asked during an interview with Diane Sawyer on PrimeTime in 2003, if "Everytime" was about Timberlake, Spears responded, "I'll let the song speak for itself."[17]

Lyrically, the song is about a brokenhearted man who moves on from his past.[26] A Rolling Stone reviewer called the song a "breakup aria".[27] According to Caroline Sullivan of The Guardian, "Cry Me a River" stands out for its "slow-building sense of drama", which highlights Timberlake at his "husky best".[28] The song begins with the phrase "You were my sun, you were my earth", which according to Timbaland was Timberlake's inspiration to write the song.[5][19] Tanya L. Edwards of MTV News observed that Timberlake was wronged and said this is demonstrated by the lyrics: "You don't have to say whatcha did / I already know, I found out from him / Now there's just no chance."[29] The chorus contains the lines: "Told me you loved me, why did you leave me all alone / Now you tell me you need me when you call me on the phone."[30]Slant Magazine's Sal Cinquemani called Timberlake's 2007 single "What Goes Around... Comes Around" an ostensible sequel to "Cry Me a River" both lyrically and musically.[31] Jason Lipshutz of Billboard stated that aside from the presence of Timbaland's "fantastically cluttered production", the difference between "Cry Me a River" and Timberlake's 2013 single "Mirrors" is clear: "10 years ago, Timberlake was broken, and now he is whole".[32]

"Cry Me A River, in all its over-sharing glory, has become a classic of its genre; a song that's able to say much more via one acoustic version than any number of media-trained interviews. It should act as the benchmark for any future pop star break-up songs."

"Cry Me a River" received acclaim from critics. Jane Stevenson of Jam! and Sal Cinquemani of Slant Magazine regarded it as a stand-out track from Justified.[20][22]Stephen Thomas Erlewine of AllMusic selected the song as a highlight in his review of Justified.[34] Peter Robinson of NME called it a "twisted epic" and "an acidic, filthy little song teeming with spite and retribution, with Timbaland's pounding."[35]Rolling Stone's Ben Ratliff viewed his production of "Cry Me a River" as exceptional.[36] Denise Boyd of BBC Music felt that the song's lyrics play as large a role as Timbaland's production, unlike other songs on Justified.[26] David Browne of Entertainment Weekly concluded that the song is "a genuine stunner" that should leave Timberlake's fellow 'N Syncers concerned that he truly may not need them any more.[25] John Mitchell of MTV News called "Cry Me a River" and "What Goes Around... Comes Around" "kiss-off songs", with Timberlake's revenge on Spears present throughout the lyrics.[37]Idolator staff opined it is the sound of an artist who is "relishing ripping up people's perceptions of him as a sweet-natured teen heartthrob."[38]VH1's Emily Exton wrote, "By stretching the boundaries of pop–and fusing it with notes of R&B, lots of electric goodness, and haunting choral vocals–Timberlake’s kiss-off song instantly becomes more poignant, a pointed reaction to the hurt he’s experienced by someone he once loved."[39] According to Complex, the song "made people completely forget about 'N Sync and start asking what Timberlake would do next."[40] The single won a Grammy Award for Best Male Pop Vocal Performance at the 2004 award ceremony.[41] It was nominated for Song of the Year at the 2003 MTV Europe Music Awards.[42][43]

For Pitchfork Media it was the 3rd best song of 2003.[44]Rolling Stone ranked "Cry Me a River" at number 20 on their list of the 100 Best Songs of the 2000s; a columnist for the magazine wrote that the real inspiration behind the song was the formation of the Timberlake–Timbaland team, "a match made in pop heaven".[45] In 2012, the magazine placed it at number 484 on their list of "The 500 Greatest Songs of All Time".[27]VH1 ranked "Cry Me a River" at number 59 on their list of the 100 Greatest Songs of the 2000s.[46]The Daily Telegraph listed the song at number 40 on the "100 songs that defined the Noughties."[47] In 2015, Spotify re-ranked Rolling Stone's 500 Greatest Songs in two different lists. "Cry Me a River" ranked at number 14 on "by all Spotify users" and 10 on "streams from millennial users".[48] In 2018, Rolling Stone ranked the song 46 on their list "The 100 Greatest Songs of the Century – So Far".[49]

"Cry Me a River" debuted at number 44 on the US Billboard Hot 100 in the issue dated December 21, 2002, earning the Hot Shot Debut honor with 29.6 million audience impressions.[50] On February 1, 2003, the single reached a peak of number three, becoming Timberlake's first solo single to reach that position.[51] The song debuted on the US Pop Songs chart at number 37 in the issue dated December 14, 2002[52] and reached a peak of three on February 1, 2003.[53] For the issue dated December 28, 2002, "Cry Me a River" debuted at number 75 on the US Hot R&B/Hip-Hop Songs chart.[54] It reached a peak of 11 on March 8, 2003.[55] It also peaked at number two on the US Hot Dance Club Songs, becoming Timberlake's second top-three song, after his debut single "Like I Love You" reached number one.[56] As of August 2003, remixes of the single have sold more than 61,000 units in the United States.[57] As of 2018, the song has sold 1.2 million copies in the country.[58]

The song debuted at number two on the Australian Singles Chart on March 9, 2003.[59] It fell to number six in the following week. "Cry Me a River" became Timberlake's first top-three solo single on the chart.[59] The song remained on the chart for 12 consecutive weeks. It was certified gold by the Australian Recording Industry Association (ARIA) for shipments of 35,000 units.[60] The single debuted at number 44 in New Zealand on March 9, 2003. After two weeks on the chart, it reached a peak of 11. It remained on the chart for 11 weeks.[61]

In the United Kingdom, "Cry Me a River", debuted at number two on February 15, 2003.[62] The next week it fell to number three, before returning to its original peak on March 1, 2003; it stayed on the chart for 13 weeks.[63] The song has sold over 365,000 copies in the country as of 2015.[64] It debuted at number 14 on the French Singles Chart on April 5, 2003. After three weeks, "Cry Me a River" peaked at number six, and it stayed on the chart for 21 weeks.[65] It was less successful on the Italian Singles Chart, where it peaked at number 14 and stayed on the chart for four weeks.[66] "Cry Me a River" also peaked at number five in Belgium (Wallonia),[67] at number six in the Republic of Ireland[68] and the Netherlands,[69] at number seven in Belgium (Flanders),[70] and at number 10 in Germany,[71] Norway,[72] and Sweden.[73]

The music video for "Cry Me a River" was directed by Francis Lawrence, and filmed in Malibu, California, during the week of October 29, 2002.[3] Lawrence created the video's concept and told MTV News, "[Justin and I] had a conversation on the phone and all he said was he wanted to have some dancing in it, but to do my thing. He told me what the song was about, but in a [general way] as well. He just said it was a kiss-off song and so I came up with this idea and he went for it".[74] Lawrence added that he also included some details in the video, including a reference to Spears's tattoo, which Timberlake enjoyed. He explained that he and Timberlake did not mention names while creating the video, only discussing the song's general beats.[74] Lawrence also revealed that executives of Jive Records were nervous about some aspects of the video, such as Timberlake's representation of a voyeur and the tone of some scenes he was portraying with a girl. "That's the thing I liked most about this project, was that he was coming into it with a super clean-cut image with 'N Sync and he's such a nice guy and so handsome and what I was into doing was making him be a bit scary. Lurking around the house in the rain, throwing a rock through her window, being a peeping Tom, getting revenge and doing stuff that's not really what a nice guy does."[74] The music video for "Cry Me a River" was released onto the iTunes Store on April 28, 2003.[75]

Timberlake stalking the blonde woman who allegedly portrays Spears inside her house

The video begins with a blonde woman, played by model and actress Lauren Hastings (allegedly portraying Britney Spears[76]), walking out of her house hand-in-hand with an unidentified man.[77] The couple leaves in the woman's car (a silver Porsche) as Timberlake rolls down the window of a black Mercedes 500 W220, from which he and his friend have been watching the woman.[74] Timberlake breaks into the house by throwing a rock through a window and proceeds through the woman's house, with anti-gravity jumps and slides, not causing any other visible damage, except for kicking a picture frame of the woman across the living room.[76] Then he searches some drawers and finds a video camera, while the driver of the car, Timbaland, signals for his female accomplice in the back of the car, played by model Kiana Bessa, to go in. She enters the house and goes with Timberlake to a bedroom, where she starts to undress and kiss him while being filmed. They stay in the bedroom for a moment; then the accomplice exits the house but Timberlake stays. As the blonde woman returns, he follows her around the house and hides in a closet as she showers. He gets closer to her and touches the glass surrounding the shower. The blonde woman senses someone in the room and turns around, but Timberlake is gone. She leaves the bathroom and goes into her bedroom, where the video he made with his new lover plays on the television.

Following the release of the music video, Us Weekly ran a cover story titled Britney Vs. Justin: The War Is On. Timberlake denied that Spears inspired the video, saying, "The video is not about her. The video is about me."[77] However, Spears told Rolling Stone in October 2003 that she received a call from Timberlake saying there would be a look-alike of her would be in a music video with him. She states that he reassured her by saying, "Don't worry about it. It's not a big deal".[82] Spears, who had not seen the video, says she allowed him to do so but became infuriated after watching it. She recalled that when she asked why he had made a video about her, he replied, "Well, I got a controversial video."[82] She stated that it was a great publicity stunt, commenting, "So he got what he wanted. I think it looks like such a desperate attempt, personally."[82] After the release of Spears' video for "Toxic" (2003), Jennifer Vineyard of MTV News said her video "[made] "Cry Me a River" look like child's play".[83]

In 2013, Billboard editor Jason Lipshutz opined the clip was "one of the more brilliant musical moments in pop music since the dawn of the century. The visual is JT's most controversial music video to date." He added, "The "Cry Me a River" video served a dual purpose for Timberlake: to court controversy, and to make its star seem more grown-up."[84] In 2018, Billboard critics named it the 24th "greatest music video of the 21st century."[85]

On October 23, 2010, while performing at the annual charity gig "Justin Timberlake and Friends" in Las Vegas, Timberlake began the show with a slow and "sultry" performance of "Cry Me a River" and segued into a cover of Bill Withers' 1971 single "Ain't No Sunshine".[91] He later resumed "Cry Me a River" before segueing into a cover of Drake's 2010 song "Over". Jillian Mapes of Billboard described the performance as "completely lovely in an effortless sort of way."[91] Timberlake performed "Cry Me a River" at concert he held during the 2013 Super Bowl weekend in New Orleans.[92] Timberlake performed "Cry Me a River" in a medley with other of his songs at the 2013 MTV Video Music Awards. After the performance he accepted a Michael Jackson Video Vanguard Award at the ceremony.[93] Timberlake included the single on the set list of his fifth worldwide concert tour, The 20/20 Experience World Tour (2013–15).[94]

"[The song] is the universal symbol of the bad celebrity break-up – more powerful than a stack of Angelina vs. Aniston tabloid covers, more effective than an official statement mailed to People magazine."

Rosalía samples the chorus from "Cry Me a River" for her song "Bagdad" on her album El mal querer (2018), featuring a Barcelona children's choir. Billboard deemed the track "a transcultural re-interpretation" of "Cry Me a River."[105]Halsey's song "Without Me" contains an interpolation of the pre-chorus of "Cry Me a River".[106]

"Cry Me a River" marked the first collaboration between Timberlake and Timbaland, and its critical and commercial success started "one of the most forward-thinking star-producer duos in pop music", as described by Variety's author Andrew Barker.[107] Alternative rock band Coldplay revealed that the single was an inspiration for the drumbeat of their song "Lost!".[108] Rock singer Marilyn Manson cited it as one of the main songs that influenced him.[109] In order to use the song in the 2017 film Lady Bird set in 2003, director Greta Gerwig sent a letter to Timberlake, "Your album Justified was that year, and it owned that year."[110]